US20080118734A1 - Coating Compositions - Google Patents

Coating Compositions Download PDF

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Publication number
US20080118734A1
US20080118734A1 US11/569,100 US56910005A US2008118734A1 US 20080118734 A1 US20080118734 A1 US 20080118734A1 US 56910005 A US56910005 A US 56910005A US 2008118734 A1 US2008118734 A1 US 2008118734A1
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Prior art keywords
materials
plasma
substrate
accordance
coating
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US11/569,100
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Inventor
Andrew James Goodwin
Stuart Robert Leadley
Liam O'Neill
Paul John Duffield
Malcolm Tom McKechnie
Simon Pugh
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RECKETT BENCKISER CORPORATE SERVICES Ltd
Dow Corning Ireland Ltd
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Dow Corning Ireland Ltd
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Assigned to DOW CORNING IRELAND LIMITED, RECKETT BENCKISER CORPORATE SERVICES, LTD. reassignment DOW CORNING IRELAND LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MCKECHNIE, MALCOLM TOM, DUFFIELD, PAUL JOHN, GOODWIN, ANDREW JAMES, LEADLEY, STUART ROBERT, O'NEILL, LIAM, PUGH, SIMON
Publication of US20080118734A1 publication Critical patent/US20080118734A1/en
Abandoned legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/62—Plasma-deposition of organic layers
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • D06M14/26—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of synthetic origin
    • D06M14/30—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of synthetic origin of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M14/32—Polyesters
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/249921—Web or sheet containing structurally defined element or component

Definitions

  • the present invention relates to a process for incorporating one or more active materials in coating compositions obtained through plasma polymerisation or plasma enhanced chemical vapour deposition (PE-CVD).
  • PE-CVD plasma enhanced chemical vapour deposition
  • Active material(s) as used herein is intended to mean one or more materials that perform one or more specific functions when present in a certain environment and in the case of the present application they are chemical species which do not undergo chemical bond forming reactions within a plasma environment. It is to be appreciated that an active material is clearly discriminated from the term “Reactive”.
  • a reactive material or chemical species is intended to mean a species which undergoes chemical bond forming reactions within a plasma environment. The active may of course be capable of undergoing a reaction after the coating process.
  • Active materials are often present in formulated products in low concentrations and yet are typically the most costly component in the formulated product.
  • the UV absorbing or refracting component of a sun block emulsion formulated product or the decongestant and/or analgesic in a cold cure formulated product Ensuring effective delivery of the active to the point of end application is a key requirement for good efficacy of the product.
  • Active materials often need to be protected during processing and prior to end use in order that they are safely released and or activated or the like at the intended point of end use for both effective performance and effective cost. This is often achieved by incorporating the active into a protective matrix, applying a protective coating, or introducing the active into a matrix in a chemically protected form (i.e. the presence of protective end groups which will react with another species in the end use environment to release the active).
  • the two former protective methods may be referred to in general terms as forms of encapsulation.
  • many pharmaceutical materials are susceptible to acidic degradation and need to be protected from the acidic stomach prior to effective release and adsorption in the more alkaline intestine.
  • the encapsulating coatings are known as enteric coatings.
  • Other additives must be protected from heat, moisture, or extremes of pH during processing as part of incorporation into the product matrix.
  • Polymeric coatings are widely used throughout industry because they are easily applied, to give conformal, filmic coatings on a wide range of substrates.
  • the functionality of the polymer for example, oil repellency, water barrier, biocompatibility, decorative, adhesive, release etc. is often provided to the substrate coated.
  • An extensive range of methods are used for the delivery and/or curing of films or the like made from the polymeric coatings.
  • a polymer melt or solution is typically applied by mechanical coating or immersion of a substrate with the resulting polymeric coating being converted to a film by a suitable curing technique such as for example by the application of heat, radiation and/or pressure.
  • PE-CVD plasma enhanced chemical vapour deposition
  • the free electrons have almost negligible mass, the total system heat content is low and the plasma operates close to room temperature thus allowing the processing of temperature sensitive materials, such as plastics or polymers, without imposing a damaging thermal burden onto the sample.
  • the hot electrons create, through high energy collisions, a rich source of radicals and excited species with a high chemical potential energy capable of profound chemical and physical reactivity.
  • Non-thermal equilibrium plasmas processes are ideal for the coating of substrates in the form of delicate and heat sensitive webbed materials because generally the resulting coatings are free of micropores even with thin layers.
  • the optical properties, e.g. colour, of the coating can often be customised and plasma coatings adhere well to even non-polar materials, e.g. polyethylene, as well as steel (e.g. anti-corrosion films on metal reflectors), textiles, etc.
  • the gases are directed so as to diffuse through plasma.
  • Any appropriate plasma may be utilised.
  • Non-thermal equilibrium plasma such as for example glow discharge plasma may be utilised.
  • the glow discharge may be generated at low pressure, i.e. vacuum glow discharge or in the vicinity of atmospheric pressure—atmospheric pressure glow discharge, however in respect of the present invention the latter is preferred.
  • Homogeneous diffuse dielectric barrier discharge such as Glow discharge plasma is generated in a gas, such as helium by a high frequency electric field.
  • the plasma is generated in a gap between two electrodes, at least one of which is encased or coated or the like in a dielectric material.
  • PE-CVD may be utilised at any suitable temperature e.g. a plasma at a temperature of from room temperature to 500° C.
  • Coulson S R Woodward I S, Badyal J P S, Brewer S A, Willis C, Langmuir, 16, 6287-6293, (2000) describe the production of highly oleophobic surfaces using long chain perfluoroacrylate or perfluoroalkene precursors.
  • Vacuum glow discharge processes have been investigated as routes to encapsulation and controlled release for example Colter, K D; Shen, M; Bell, A T Biomaterials, Medical Devices, and Artificial Organs (1977), 5(1), 13-24 describes a method where fluoropolymer coatings are applied to reduce the diffusion of a steroid active through a polydimethylsiloxane elastomer.
  • Kitade, Tatsuya; Kitamura, Keisuke; Hozumi, Kei. Chemical & Pharmaceutical Bulletin (1987), 35(11), 4410-17 describes the application of vacuum glow discharge plasma to coat a powdered active with a PTFE based coating for controlled dissolution.
  • WO 9910560 describes a further vacuum plasma method where precursor vapour is introduced to the plasma to produce coatings for the purpose of encapsulation.
  • diffuse dielectric barrier discharge one form of which can be referred to as an atmospheric pressure glow discharge Sherman, D. M. et al, J. Phys. D.; Appl. Phys. 2005, 38 547-554.
  • This term is generally used to cover both glow discharges and dielectric barrier discharges whereby the breakdown of the process gas occurs uniformly across the plasma gap resulting in an homogeneous plasma across the width and length of a plasma chamber.
  • Atmospheric pressure diffuse dielectric discharge processes such as Atmospheric Pressure Glow Discharge (APGD) offer an alternative homogeneous plasma source, which have many of the benefits of vacuum plasma methods, while operating at atmospheric pressure or thereabouts.
  • APGD Atmospheric Pressure Glow Discharge
  • WO 01 59809 and WO 02 35576 describe a series of wide area APGD systems, which provide a uniform, homogeneous plasma at ambient pressure by application of a low frequency RF voltage across opposing parallel plate electrodes separated by ⁇ 10 mm. The ambient pressure and temperature ensures compatibility with open perimeter, continuous, on-line processing.
  • the plasma utilised is at substantially atmospheric pressure.
  • the plasma is generated at any suitable temperature, it preferably operates at a temperature between room temperature (20° C.) and 300° C. and typically, in the case of diffuse dielectric barrier discharge processes, is utilized at a temperature in the region of 30 to 50° C. Whilst the temperature of activated electrons may be individually >1000° C., the system as a whole must operate at a temperature sufficiently low not to disintegrate or deactivate either the trapped active species or the coating material which in many cases are heat sensitive. Hence the process cannot be carried out at high temperatures using, for example, flame treatment systems (thermal equilibrium plasmas) which operate at significantly greater than 300° C., i.e. >1000° C. gas temperature.
  • Therapeutically active materials which may be employed include, for example, anti-acne agent, antibiotic, antiseptic, anti-fungal, anti-bacterial, anti-microbial, biocides, anti-inflammatory, hyluronic acid containing materials, astringents, hormones, anti-cancer agents, smoking cessation compositions, cardiovascular, histamine blocker, bronchodilator, analgesic, anti-arrythmic, anti-histamine, alpha-I blocker, beta blocker, ACE inhibitor, diuretic, anti-aggregant, sedative, tranquilizer, anti-convulsant, anti-coagulant agents, vitamins, anti-aging agents, agents for treating gastric and duodenal ulcers, anti-cellulites, proteolytic enzymes, healing factors, cell growth nutrients, peptides and others.
  • anti-acne agent antibiotic, antiseptic, anti-fungal, anti-bacterial, anti-microbial, biocides, anti-inflammatory, hyluronic acid containing materials
  • Suitable therapeutic active materials include penicillins, cephalosporins, tetracyclines, macrolides, epinephrine, amphetamines, aspirin, acetominophen, barbiturates, catecholamines, benzodiazepine, thiopental, codeine, morphine, procaine, lidocaine, benzocaine, sulphonamides, ticonazole, perbuterol, furosamide, prazosin, prostaglandins, salbutamol, indomethicane, diclofenac, glafenine, dipyridamole, theophylline and retinol.
  • cellulose derivatives cellulose derivatives, gelatin, xanthan gum, natural gums), imidazolines, inorganic materials (clay, TiO2, ZnO), ketones (e.g. camphor), isothionates, lanolin and derivatives, organic salts, phenols including salts (e.g. parabens), phosphorus compounds (e.g. phosphate derivatives), polyacrylates and acrylate copolymers, protein and enzymes derivatives (e.g. collagen), synthetic polymers including salts, siloxanes and silanes, sorbitan derivatives, sterols, sulphonic acids and derivatives and waxes.
  • inorganic materials clay, TiO2, ZnO
  • ketones e.g. camphor
  • isothionates lanolin and derivatives
  • organic salts phenols including salts (e.g. parabens), phosphorus compounds (e.g. phosphate derivatives), polyacrylates and acrylate copolymers
  • anti-acne materials which may be utilized as the active material in a composition in accordance with the present invention, include Salicylic acid and Sulphur.
  • Some examples of anti-fungal materials are Calcium Undecylenate, Undecylenic Acid, Zinc Undecylenate, and Povidone-Iodine.
  • Some examples of anti-microbial materials are Alcohol, Benzalkonium Chloride, Benzethonium Chloride, Methylbenzethonium Chloride, Phenol, Poloxamer 188, and Povidone-Iodine.
  • antioxidants which may be utilized as the active material in a composition in accordance with the present invention include Acetyl Cysteine, Arbutin, Ascorbic Acid, Ascorbic Acid Polypeptide, Ascorbyl Dipalmitate, Ascorbyl Methylsilanol Pectinate, Ascorbyl Palmitate, Ascorbyl Stearate, BHA, p-Hydroxyanisole, BHT, t-Butyl Hydroquinone, Caffeic Acid, Camellia Sinensis Oil, Chitosan Ascorbate, Chitosan Glycolate, Chitosan Salicylate, Chlorogenic Acids, Cysteine, Cysteine HCl, Decyl Mercaptomethylimidazole, Erythorbic Acid, Diamylhydroquinone, Di-t-Butylhydroquinone, Dicetyl Thiodipropionate, Dicyclopentadiene/t-Butylcresol Copolymer, Digalloyl
  • biocides are Aluminium Phenolsulphonate, Ammonium Phenolsulphonate, Bakuchiol, Benzalkonium Bromide, Benzalkonium Cetyl Phosphate, Benzalkonium Chloride, Benzalkonium Saccharinate, Benzethonium Chloride, Potassium Phenoxide, Benzoxiquine, Benzoxonium Chloride, Bispyrithione, Boric Acid, Bromochlorophene, Camphor Benzalkonium Methosulphate, Captan, Cetalkonium Chloride, Cetearalkonium Bromide, Cetethyldimonium Bromide, Cetrimonium Bromide, Cetrimonium Chloride, Cetrimonium Methosulphate, Cetrimonium Saccharinate, Cetrimonium Tosylate, Cetylpyridinium Chloride, Chloramine T, Chlorhexidine, Chlorhexidine Diacetate, Chlorhexidine Digluconate
  • External analgesics which may be utilized as the active material in a composition in accordance with the present invention include Benzyl Alcohol, Capsicum Oleoresin (Capsicum Frutescens Oleoresin), Methyl Salicylate, Camphor, Phenol, Capsaicin, Juniper Tar (Juniperus Oxycedrus Tar), Phenolate Sodium (Sodium Phenoxide), Capsicum (Capsicum Frutescens), Menthol, Resorcinol, Methyl Nicotinate, and Turpentine Oil (Turpentine).
  • Benzyl Alcohol Capsicum Oleoresin
  • Capsicum Frutescens Oleoresin Capsicum Frutescens Oleoresin
  • Methyl Salicylate Camphor
  • Phenol Capsaicin
  • Juniper Tar Juniperus Oxycedrus Tar
  • Phenolate Sodium Sodium Phenoxide
  • Capsicum Capsicum Frut
  • oxidizing materials which may be utilized as the active material in a composition in accordance with the present invention include Ammonium Persulphate, Potassium Bromate, Potassium Caroate, Potassium Chlorate, Potassium Persulphate, Sodium Bromate, Sodium Chlorate, Sodium Iodate, Sodium Perborate, Sodium Persulphate and, Strontium Dioxide.
  • An example of a skin bleaching material which may be utilized as the active material in a composition in accordance with the present invention includes Hydroquinone.
  • Some examples of skin protectants which may be utilized as the active material in a composition in accordance with the present invention include Allantoin, Aluminium Acetate, Aluminium Hydroxide, Aluminium Sulphate, Calamine, Cocoa Butter, Cod Liver Oil, Colloidal Oatmeal, Dimethicone, Glycerin, Kaolin, Lanolin, Mineral Oil, Petrolatum, Shark Liver Oil, Sodium Bicarbonate, Talc, Witch Hazel, Zinc Acetate, Zinc Carbonate, and Zinc Oxide.
  • the active material may comprise one or more pesticides, herbicides and/or fungicides including for example Amide Herbicides such as allidochlor N,N-diallyl-2-chloroacetamide; CDEA 2-chloro-N,N-diethylacetamide; etnipromid (RS)-2-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]-N-ethylpropionamide; anilide herbicides such as cisanilide cis-2,5-dimethylpyrrolidine-1-carboxanilide; flufenacet 4′-fluoro-N-isopropyl-2-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yloxy]acetanilide; naproanilide (RS)- ⁇ -2-naphthoxypropionanilide; arylalanine herbicides such as benzoylprop N-benzoyl-N-(3,4-
  • Flame retardants may also be included as the active material. These include for example Halogen based flame-retardants such as decabromodiphenyloxide, octabromordiphenyl oxide, hexabromocyclododecane, decabromobiphenyl oxide, diphenyoxybenzene, ethylene bis-tetrabromophthalmide, pentabromoethyl benzene, pentabromobenzyl acrylate, tribromophenyl maleic imide, tetrabromobisphenyl A and derivatives thereof, bis-(tribromophenoxy)ethane, bis-(pentabromophenoxy)ethane, polydibomophenylene oxide, tribromophenylallyl ether, bis-dibromopropyl ether, tetrabromophthalic anhydride and derivatives, dibromoneopentyl gycol, dibromoethyl dibro
  • Phosphorous based flame-retardants such as (2,3-dibromopropyl)-phosphate, phosphorous, cyclic phosphates, triaryl phosphate, bis-melaminium pentate, pentaerythritol bicyclic phosphate, dimethyl methyl phosphate, phosphine oxide diol, triphenyl phosphate, tris-(2-chloroethyl)phosphate, phosphate esters such as tricreyl, trixylenyl, isodecyl diphenyl, ethylhexyl diphenyl, Phosphate salts of various amines such as ammonium phosphate, trioctyl, tributyl or tris-butoxyethyl phosphate ester.
  • Phosphorous based flame-retardants such as (2,3-dibromopropyl)-phosphate, phosphorous, cyclic phosphate
  • flame retardant active materials may include tetraalkyl lead compounds such as tetraethyl lead, iron pentacarbonyl, manganese methyl cyclopentadienyl tricarbonyl, melamine and derivatives such as melamine salts, guanidine, dicayandiamide, silicones such as poldimethylsiloxanes, ammonium sulphamate, alumina trihydrate, and magnesium hydroxide Alumina trihydrate.
  • tetraalkyl lead compounds such as tetraethyl lead, iron pentacarbonyl, manganese methyl cyclopentadienyl tricarbonyl, melamine and derivatives such as melamine salts, guanidine, dicayandiamide, silicones such as poldimethylsiloxanes, ammonium sulphamate, alumina trihydrate, and magnesium hydroxide Alumina trihydrate.
  • Catalysts which may be utilized as the active material in a composition in accordance with the present invention may include particles that contain metals such as Pt, Rh, Ir, Ag, Au, Pd, Cu, Ru, Ni, Mg, Co or other catalytically active metals. Mixtures of metals such as Pt—Rh, Rh—Ag, V—Ti or other well known mixtures may also be used.
  • the metal may exist in its elemental state, as a fine powder, or as a complex such as a metallocene, chloride, carbonyl, nitrate or other well known forms.
  • non-metallic catalysts may be used.
  • non-metallic catalysts include sulphuric acid, acetic acid, sodium hydroxide or phosphoric acids.
  • the coating derived from the coating forming material may be a simple polymer designed to disperse and entrap active material and in the case where the active material is (e.g. a catalyst), or it may act to promote the activity of the catalyst material through well-known catalyst support interactions.
  • Suitable silicon-containing materials for use in the method of the present invention include silanes (for example, silane, alkylsilanes, alkylhalosilanes, alkoxysilanes) and linear (for example, polydimethylsiloxane) and cyclic siloxanes (for example, octamethylcyclotetrasiloxane), including organo-functional linear and cyclic siloxanes (for example, Si—H containing, halo-functional, and haloalkyl-functional linear and cyclic siloxanes, e.g. tetramethylcyclotetrasiloxane and tri(nonofluorobutyl)trimethylcyclotrisiloxane).
  • a mixture of different silicon-containing materials may be used, for example to tailor the physical properties of the substrate coating for a specified need (e.g. thermal properties, optical properties, such as refractive index, and viscoelastic properties).
  • the substrate may be in the form of a flat web (film, paper, fabric, non-woven, metallic foil, powder and moulded or engineered components or extruded forms such as tubes and ribbons.
  • Powders may include, for example any suitable material, for example metals, metal oxides, silica and silicates, carbon, organic powdered substrates, mineral fillers such as for example carbon black, clays, CaCO 3 , talc, silica, mica conductive fillers, TiO 2 nanoparticles, metal oxides such as TiO2, ZrO 2 , Fe 2 O 3 Al 2 O 3 SiO 2 , B 2 O 3 , Li 2 O, Na 2 O, PbO, ZnO, or, CaO, Pb 3 O 4 and CuO and mixed oxides, graphite, phosphorus particles, pigments and the like; metalloid oxides, mixed oxide, organometallic oxides, organometalloid oxides, organomixed oxide resins and/or an organic resin, sodium carbonate potassium nitrate
  • the textiles may comprise Clothing (sports, leisure, medical and/or military); Non-woven materials e.g. medical drape & clothing filter means for liquids and separations of for example water, food and beverages applications, or medical applications.); air filtration means for air conditioning and ventilation, automotive, clean room, sterile room (industrial & medical); and Cosmetic wipes.
  • Clothing sports, leisure, medical and/or military
  • Non-woven materials e.g. medical drape & clothing filter means for liquids and separations of for example water, food and beverages applications, or medical applications.
  • air filtration means for air conditioning and ventilation, automotive, clean room, sterile room (industrial & medical)
  • Cosmetic wipes for Cosmetic wipes.
  • Wound care including bandages, plasters, casts, wound dressings, adhesive tapes, gels, pastes, pads, gauzes, swabs, tissue engineered products (e.g. biosynthetic, human-based tissue based dressings) drug delivery formulations (including transdermal patches, topical patches, medicated bandages, implantable pump, implants and inserts) and biomaterials, medical devices (including stents, shunts, ostomy devices, blood collection pouches), surgical drapes, catheters and tubings, contact lenses, surgical implants, prosthesis; oral care devices including floss, bristles, toothpick, adhesive strips (e.g. whitening), swabs and tablets and sticks (e.g. chewing gum).
  • tissue engineered products e.g. biosynthetic, human-based tissue based dressings
  • drug delivery formulations including transdermal patches, topical patches, medicated bandages, implantable pump, implants and inserts
  • biomaterials including stents, shunts, ost
  • An additional advantage of this method is that diffusion of the active from the coating may be controlled by the properties of the plasma coating. Diffusion is hindered by increased cross-linking, which may give rise to controlled release properties. Diffusion may also be hindered to the point where active is not released from the coating, either by increasing the cross-link density or over coating with a barrier coating.
  • An advantage of the present invention over the prior art is that both liquid and solid atomised coating-forming materials may be used to form substrate coatings, due to the method of the present invention taking place under conditions of atmospheric pressure. Furthermore the coating-forming materials can be introduced into the plasma discharge or resulting stream in the absence of a carrier gas, i.e. they can be introduced directly by, for example, direct injection, whereby the coating forming materials are injected directly into the plasma.
  • the homogeneous plasma is generated between a pair of electrodes within a gap of from 3 to 50 mm, for example 5 to 25 mm.
  • the present invention has particular utility for coating films, fibres and powders.
  • the generation of steady-state homogeneous diffuse dielectric barrier discharge such as glow discharge plasma at atmospheric pressure is preferably obtained between adjacent electrodes that may be spaced up to 5 cm apart, dependent on the process gas used.
  • the electrodes being radio frequency energised with a root mean square (rms) potential of 1 to 100 kV, preferably between 1 and 30 kV at 1 to 100 kHz, preferably at 15 to 50 kHz.
  • the voltage used to form the plasma will typically be between 1 and 30 kVolts, most preferably between 2.5 and 10 kV however the actual value will depend on the chemistry/gas choice and plasma region size between the electrodes.
  • Each electrode may comprise a metal plate or metal gauze or the like retained in a dielectric material or may, for example, be of the type described the applicants co-pending application WO 02/35576 wherein there are provided electrode units containing an electrode and an adjacent a dielectric plate and a cooling liquid distribution system for directing a cooling conductive liquid onto the exterior of the electrode to cover a planar face of the electrode.
  • Each electrode unit comprises a watertight box having one side in the form of a dielectric plate to which a metal plate or gauze electrode is attached on the inside of the box.
  • each electrode may be of the type described the applicants co-pending application No WO 2004/068916 which was published after the priority date of the present application.
  • each electrode comprises a housing having an inner and outer wall, wherein at least the inner wall is formed from a dielectric material, and which housing contains an at least substantially non-metallic electrically conductive material in direct contact with the inner wall instead of the “traditional” metal plate or mesh. Electrodes of this type are preferred because the inventors have identified that by using electrodes in accordance with the present invention to generate a diffuse dielectric barrier discharge, the resulting homogeneous plasma can be generated with reduced inhomogeneities when compared to systems utilizing metal plate electrodes. A metal plate is never fixed directly to the inner wall of an electrode in the present invention and preferably, the non-metallic electrically conductive material is in direct contact with the inner wall of the electrode.
  • Dielectric materials referred to in the present application may be of suitable type examples include but are not restricted to polycarbonate, polyethylene, glass, glass laminates, epoxy filled glass laminates and the like.
  • the dielectric has sufficient strength in order to prevent any bowing or disfigurement of the dielectric by the conductive material in the electrode.
  • the dielectric used is machinable and is provided at a thickness of up to 50 mm in thickness, more preferably up to 40 mm thickness and most preferably 15 to 30 mm thickness. In instances where the selected dielectric is not sufficiently transparent, a glass or the like window may be utilized to enable diagnostic viewing of the generated plasma.
  • the electrodes may be spaced apart by means of a spacer or the like, which is preferably also made from a dielectric material which thereby effects an increase in the overall dielectric strength of the system by eliminating any potential for discharge between the edges of the conductive liquid.
  • the substantially non-metallic electrically conductive material may be in the form of one or more conductive polymer compositions, which may typically be supplied in the form of pastes.
  • pastes are currently used in the electronics industry for the adhesion and thermal management of electronic components, such as microprocessor chip sets. These pastes typically have sufficient mobility to flow and conform to surface irregularities.
  • Suitable polymers for the conductive polymer compositions in accordance with the present invention may include silicones, polyoxypolyeolefin elastomers, a hot melt based on a wax such as a, silicone wax, resin/polymer blends, silicone polyamide copolymers or other silicone-organic copolymers or the like or epoxy, polyimide, acrylate, urethane or isocyanate based polymers.
  • the polymers will typically contain conductive particles, typically of silver but alternative conductive particles might be used including gold, nickel, copper, assorted metal oxides and/or carbon including carbon nanotubes; or metallised glass or ceramic beads.
  • an atmospheric pressure plasma assembly comprising a first and second pair of parallel spaced-apart electrodes in accordance with the present invention, the spacing between inner plates of each pair of electrodes forming a first and second plasma zone wherein the assembly further comprises a means of transporting a substrate successively through said first and second plasma zones and an atomiser adapted to introduce an atomised liquid or solid coating making material into one of said first or second plasma zones.
  • the electrodes are vertically arrayed.
  • An alternative means of generating the required plasma for the present invention is by means of an atmospheric pressure plasma jet (APPJ).
  • An APPJ is a non-thermal equilibrium plasma. This consists of a one electrode (a needle form) or two electrode form i.e. concentric electrodes over which or between which respectively a process gas e.g. helium is supplied.
  • a plasma is ignited and the ionised/excited gas generated by the plasma is directed through a nozzle and onto a substrate a short distance from the nozzle tip.
  • the plasma produced by an APPJ system is directed from the space between the electrodes (the plasma zone) as a flame-like phenomenon and can be used to treat remote objects.
  • a number of alternative designs for plasma jet systems suitable for use in the present invention when supplied with a suitable atomiser are described below with the assistance of the Figures.
  • the coating-forming material may be atomised using any conventional means, for example an ultrasonic nozzle.
  • the material to be atomised is preferably in the form of a liquid, or a liquid/solid slurry.
  • the atomiser preferably produces a coating-forming material drop size of from 10 to 100 ⁇ m, more preferably from 10 to 50 ⁇ m.
  • Preferred atomisers include, for example, ultrasonic nozzles, pneumatic or vibratory atomisers in which energy is imparted at high frequency to the liquid.
  • the vibratory atomisers may use an electromagnetic or piezoelectric transducer for transmitting high frequency oscillations to the liquid stream discharged through an orifice. These tend to create substantially uniform droplets whose size is a function of the frequency of oscillation.
  • Suitable ultrasonic nozzles which may be used include ultrasonic nozzles from Sono-Tek Corporation, Milton, N.Y., USA or Lechler GmbH of Metzingen Germany.
  • Other suitable atomisers which may be utilised include gas atomising nozzles, pneumatic atomisers, pressure atomisers and the like.
  • the apparatus of the present invention may include a plurality of atomisers, which may be of particular utility, for example, where the apparatus is to be used to form a copolymer coating on a substrate from two different coating-forming materials, where the monomers are immiscible or are in different phases, e.g. the first is a solid and the second is gaseous or liquid.
  • the active material is introduced into the system using the same atomiser(s) with which the coating forming material is introduced.
  • the active material may be introduced into the system via a second or second series of atomisers or other introducing means, preferably simultaneously with the introduction of the coating-forming material.
  • Any suitable alternative introducing means may be utilised such as for example compressed gas and/or gravity feed powder feeders.
  • a carrier gas any suitable carrier gas may be utilised although helium is preferred.
  • the process gas used to generate a plasma suitable for use in the present invention may be any suitable gas but is preferably an inert gas or inert gas based mixture such as, for example helium, argon, nitrogen and mixtures comprising at least one of the preceding gases, such as, a mixture of helium and argon or an argon based mixture additionally containing ketones and/or related compounds.
  • These process gases may be utilized alone or in combination with potentially reactive gases such as, for example, ammonia, O 2 , H 2 O, NO 2 , air or hydrogen.
  • the process gas will be Helium alone or in combination with an oxidizing or reducing gas. The selection of gas depends upon the plasma processes to be undertaken. When an oxidizing or reducing process gas is required, it will preferably be utilized in a mixture comprising 90-99% noble gas and 1 to 10% of oxidizing or reducing gas.
  • the present method may be used to form an oxygen containing coating on the substrate.
  • silica-based coatings can be formed on the substrate surface from atomised silicon-containing coating-forming materials.
  • the present method may be used to form oxygen free coatings, for example, silicon carbide based coatings may be formed from atomised silicon containing coating forming materials.
  • nitrogen can bind to the substrate surface, and in an atmosphere containing both nitrogen and oxygen, nitrates can bind to and/or form on the substrate surface.
  • gases may also be used to pre-treat the substrate surface prior to exposure to a coating forming substance.
  • oxygen containing plasma treatment of the substrate may provide improved adhesion between the substrate and the applied coating with oxygen containing plasma being generated by introducing oxygen containing materials, such as oxygen gas or water, to the plasma.
  • the coated substrate of the present invention may be coated with a plurality of layers of differing composition. These may be applied by passing the substrate relative to a plurality of plasma regions or by repeatedly passing the substrate or partially coated substrate repeatedly relative to the plasma regions. Where appropriate the substrate or the plasma system may move relative to the other. Any suitable number of cycles or plasma zones may be utilised in order to achieve the appropriate multi-coated substrates.
  • the substrate may pass through a plasma zone, adjacent a plasma zone through or remote from the excited gas stream or even remote thereof such that the substrate may be maintained outside the region affected by the plasma and/or excited gas stream.
  • a single plasma assembly may be utilised with a means for varying the materials passing through the plasma zone formed between the electrodes.
  • the only substance passing through the plasma zone might be the process gas such as helium which is excited by the application of the potential between the electrodes to form a plasma zone.
  • the resulting helium plasma may be utilised to clean and/or activate the substrate that is passed through or relative to the plasma zone.
  • one or more coating forming precursor material(s) and the active material may be introduced and the one or more coating forming precursor material(s) are excited by passing through the plasma zone and treating the substrate.
  • the substrate may be moved through or relative to the plasma zone on a plurality of occasions to effect a multiple layering and where appropriate the composition of the coating forming precursor material(s) may be varied by replacing, adding or stopping the introduction of one or more for example introducing one or more coating forming precursor material(s) and/or active materials.
  • any suitable non-thermal equilibrium plasma equipment may be used to undertake the method of the present invention, however atmospheric pressure diffuse dielectric barrier discharge generating equipment or low pressure glow discharge, which may be operated in either continuous mode or pulse mode are preferred.
  • the plasma equipment may also be in the form of an APPJ as described in WO 03/085693. Where the substrate is placed downstream and remote from the plasma source.
  • any conventional means for generating an atmospheric pressure diffuse dielectric barrier discharge such as a glow discharge may be used in the method of the present invention, for example atmospheric pressure plasma jet, atmospheric pressure microwave glow discharge and atmospheric pressure glow discharge.
  • a glow discharge may be used in the method of the present invention, for example atmospheric pressure plasma jet, atmospheric pressure microwave glow discharge and atmospheric pressure glow discharge.
  • such means will employ helium, argon or nitrogen or mixtures containing at least one of the latter as the process gas, although a helium process gas is preferred and a high frequency (e.g. >1 kHz) power supply to generate a homogeneous diffuse dielectric barrier discharge.
  • the process gas for forming the plasma may be as described for the atmospheric pressure system but may alternatively not comprise noble gases such as helium and/or argon and may therefore purely be oxygen, air or an alternative oxidising gas.
  • FIGS. 4 to 7 are alternative designs for plasma jet equipment which may be utilised in the present invention.
  • precursor solutions comprising the coating-forming material and the active materials were then deposited onto polypropylene and polyester fabric substrates using a diffuse dielectric barrier discharge assembly of the type shown in FIG. 1 .
  • the flexible polypropylene and polyester fabric substrate was transported through the plasma assembly by means of guide rollers 70 , 71 and 72 .
  • a helium process gas inlet 75 , an assembly lid 76 and an ultrasonic nozzle 74 for introducing atomised precursor solutions into plasma region 60 are provided.
  • Plasma power used in both plasma regions varied between 0.4 and 1.0 kW.
  • a 100 mm wide web of flexible substrate was transported through the plasma assembly at a speed of speed was varied between 1 and 4 mmin ⁇ 1 .
  • the substrate was initially directed to and over guide roller 70 through plasma region 25 between electrodes 20 a and 26 .
  • the plasma generated between electrodes 20 a and 26 in plasma region 25 was utilised as a cleaning helium plasma, i.e. no reactive material is directed into plasma region 25 .
  • Helium was introduced into the system by way of inlet 75 .
  • Lid 76 is placed over the top of the system to prevent the escape of helium, as it is lighter than air.
  • Plasma region 60 Upon leaving plasma region 25 the plasma cleaned substrate passes over guide 71 and is directed down through plasma region 60 , between electrodes 26 and 20 b and over roller 72 .
  • Plasma region 60 however is utilised to coat the substrate with plasma treated precursor solution introduced in a liquid form through ultrasonic nozzle introduced at a rate of between 25-50 ⁇ Lmin ⁇ 1 .
  • the precursor solution is itself plasma treated when passing through plasma region 60 generating a coating for the substrate in which the active materials are retained.
  • the coated substrate then passes through plasma region 60 and is coated and then is transported over roller 72 and is collected or further treated with additional plasma treatments.
  • Rollers 70 and 72 may be reels as opposed to rollers. Having passed through is adapted to guide the substrate into plasma region 25 and on to roller 71 .
  • XPS X-ray Photoelectron Spectroscopy
  • Anti-microbial testing was carried out using a modified version of ISO846 norm (“Plastics—Evaluation of the action of microorganisms”). Fabric and plastic samples were exposed to a mixed suspension of fungal spores in the presence of a complete medium, for a specified period of time (4 weeks) and in specified conditions of temperature (28° C. ⁇ 1° C.) and humidity. The dishes were examined every 2 days in order to ensure spore viability. The final and official examination is performed after 4 incubation weeks. The broad spectrum efficiency of a material is determined by the “growth rating” scale from 0 to 5, in Table 3. This scale measured the extent to which visible fungal growth is inhibited on the material sample being tested.
  • FIG. 2 a shows a representative carbon (C 1s) spectrum for polymerised acrylic acid based precursors.
  • the C 1s spectrum shows both C—C chains and retention of COOH functionality. Some oxidation of the precursor was also observed, resulting in the presence of small quantities of C—O and C ⁇ O species. Investigation of the high resolution C1s spectra revealed very similar chemistry to that previously reported for acrylic acid derived plasma coatings. Compositional analysis for each sample is included in Table 4.
  • FIG. 2 b shows a C 1s spectrum for a PEG acrylate based coating, displaying good retention of glycol functionality. The carbon chemistry for these samples may be found in Table 6.
  • FIG. 2 a shows a typical spectrum for polymerised salts in acrylic acid.
  • the nitrogen (N 1s) core level shows a peak in the region of 398-404 eV. Fitting synthetic peaks to the core level required two overlapping peaks.
  • the main peak at ⁇ 402 eV is attributed to nitrogen in a quaternary ammonium structure.
  • the second peak at ⁇ 400 eV is attributed to a neutral NR 3 chemistry.
  • the relative concentration of the quaternary ammonium salts was found to vary between 45 and 73% of the total N content, as is evident from Table 5 and 7.
  • samples were cut from the coated films and subjected to a variety of wash tests. Samples were washed in NaOH (aq) -pH 12, Water-pH 7 and HCl (aq) -pH 2.
  • Cetyl pyridinium chloride in acrylic acid coatings is very stable to water washing, indicating good entrapment of the surfactant.
  • the —NR 3 + is partially deprotonated, indicating that only ca. 40% of the —NR 3 + is susceptible to alkali attack at the surface. This may be due to either the physical properties of the coating or the dissociation constants of the ammonium cation.
  • the —NR 3 + reverts completely to —NR 2 on acid washing.
  • a similar effect is observed for benzalkonium chloride in acrylic acid where it is partially converted to —NR 2 on alkali wash, with nearly full reversion to —NR 3 + on acid wash.
  • the PEG based coatings were less susceptible to damage from the washing treatments.
  • the sodium hydroxide altered the chemistry of the nitrogen component, but had limited effect on the PEG polymer.
  • Water washing also had little effect.
  • the HCl wash did have a dramatic effect on the C—O functionality, with most of the C—O species disappearing, as is evident from Table 12.
  • this cell skin was removed and the surface of fabric was analysed by stereomicroscopy. No trace of spores and mycelium was detected between stitches of treated and untreated fabric. All fabric samples presented a clean surface after removing the mould skin, because polyester is not an appropriate nutrient source for microorganisms.
  • FIG. 4 relates to a Single electrode design plasma jet system.
  • This design consists of a tube ( 7 ), surrounded by a suitable dielectric material ( 8 ).
  • the process gas enters an opening ( 6 ).
  • a single electrode ( 5 ) is placed outside the tube and this is encased in a layer the dielectric material ( 8 ).
  • the electrode is connected to a suitable power supply. No counter electrode is required. When power is applied, local electric fields form around the electrode. These interact with the gas within the tube and a plasma is formed, which exits through an aperture ( 9 )
  • FIG. 5 relates to an alternative plasma jet electrode design.
  • a single sharp electrode is housed within a plastic tube through which the aerosol and process gas flow.
  • an electric field forms and the process gas is ionised, as in the previous design.
  • a 6 mm pipe is included at the exit of the plasma to maintain the laminar flow of the plasma gas. This acts to minimise entrainment of air, which would quench the plasma jet after it leaves the device.
  • This design it is possible to produce plasma jets using a range of process gases, to include helium, argon, oxygen, nitrogen, air and mixtures of said gases.
  • This chamber may be constructed from a suitable dielectric material such as polytetrafluoroethylene.
  • the process gas and precursors enter into the chamber through one or more apertures ( 11 ) in the housing.
  • the process gas becomes ionised, and the resultant plasma is directed out through an opening ( 14 ).
  • the size, shape and length of the plasma flame can be adjusted.
  • FIG. 6 depicts an alternative design in which the aerosol and process gas enter upstream ( 15 ) of the plasma.
  • the aerosol is introduced directly into the plasma. This is achieved by having a second gas entry point ( 16 ) located close to the tip of the electrode ( 17 ). The aerosol can be added directly at this point ( 16 ), with the main process gas still entering upstream of the plasma region ( 15 ). Alternatively, some (or all) of the process gas can also be added with the aerosol adjacent to the tip of the electrode. Using this setup, the plasma and precursor exit though a suitable opening ( 18 ).
  • FIG. 7 depicts a preferred device for the treatment of the inside of 3-D objects and or tubes and or conducting substrates has also been developed which generates long plasmas.
  • a powered electrode ( 19 ) interacts with a process gas ( 20 ) and aerosol ( 21 ) to produce a plasma.
  • the length of the plasma can be extended by confining the plasma to a tube ( 22 ) as it leaves the device. As long as the plasma is confined within this tube, then the plasma is not quenched by interaction with the external atmosphere.
  • conductive pieces ( 23 ) may be inserted into the tube. The resulting plasma may be extended over considerable distance before exiting through a suitable opening ( 24 ).
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